Portable media players have become commonplace in today's society. When a user desires to transfer new media content, such as songs or videos, to his or her portable media player, the user must manually select the media content from his or her media collection stored on an associated personal computer. The issue with this traditional method for selecting and transferring media content to a portable media player is that the user must dedicate a significant amount of time to sitting at his or her personal computer. In today's busy world, this is not desirable. Thus, there is a need for a system and method for providing previews of a user's media collection to the user's portable media player. There is further a need for a system and method of selecting desired ones of the previews on the user's portable media player and transferring corresponding media files to the user's portable media player.